Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

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2:12 minutes

Problem 36a

Textbook Question

Predict the major products of the following reactions:
(a)

Verified step by step guidance

Step 1: Recognize the reaction type. The reagents Zn(Hg), HCl, and H2O indicate a Clemmensen reduction, which is used to reduce ketones or aldehydes to alkanes.

Step 2: Identify the functional group in the starting material. The given compound contains a ketone group attached to a benzene ring and an ethyl chain.

Step 3: Understand the mechanism. In Clemmensen reduction, the ketone group is reduced to a methylene (-CH2-) group, effectively removing the oxygen atom and saturating the carbon with hydrogen atoms.

Step 4: Predict the structural change. The ketone group in the starting material will be replaced by a methylene group, resulting in a compound where the benzene ring is directly attached to the ethyl chain.

Step 5: Draw the major product. The final structure will consist of a benzene ring connected to an ethyl chain without the ketone group. Ensure the connectivity and saturation of the molecule are correct.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Clemmensen Reduction

The Clemmensen reduction is a chemical reaction that reduces carbonyl compounds, such as aldehydes and ketones, to their corresponding alkanes using zinc amalgam (Zn(Hg)) in the presence of hydrochloric acid (HCl). This reaction is particularly useful for converting aromatic ketones into aliphatic hydrocarbons, effectively removing the carbonyl functional group.

Aromatic Compounds

Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized π-electrons, which follow Huckel's rule (4n + 2 π electrons). These compounds, such as benzene and its derivatives, exhibit unique reactivity patterns, including electrophilic substitution, which is crucial for understanding their behavior in various chemical reactions.

Electrophilic Substitution

Electrophilic substitution is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom in an aromatic ring. This process is essential for modifying aromatic compounds, allowing for the introduction of various functional groups while maintaining the aromaticity of the ring. Understanding this mechanism is key to predicting the products of reactions involving aromatic systems.

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